Formaldehyde → HCID 70094222, compound

HRID 343332Notes

Reaction equation

HRID 343332 reaction equation
C=O.[CH2:3]([O:5][C:6]([C@H:8]1[CH2:13][C:12]([CH3:14])=[CH:11][CH2:10][N:9]1[C:15](=[O:40])[C@H:16]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[N:39])[CH:33]=1)[NH:17][S:18]([C:21]1[CH:30]=[C:29]2[C:24]([CH2:25][CH2:26][NH:27][CH2:28]2)=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:7])[CH3:4].[C:41](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:3]([O:5][C:6]([C@H:8]1[CH2:13][C:12]([CH3:14])=[CH:11][CH2:10][N:9]1[C:15](=[O:40])[C@H:16]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[N:39])[CH:33]=1)[NH:17][S:18]([C:21]1[CH:30]=[C:29]2[C:24]([CH2:25][CH2:26][N:27]([CH3:41])[CH2:28]2)=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70081162HCID 70081162, compound

Product 1

HCID 70094222HCID 70094222, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aqueous formaldehyde solution (37% w/v, 1.4 ml, 17.3 mmol) was added to a stirred solution of 4-methyl-1-[N-(1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanyl]-1,2,3,6-tetrahydropyridine-2(R)-carboxylic acid ethyl ester (Preparation 45; 2.26 g, 4.2 mmol) in dichloromethane (30 ml). After 0.75 hour, sodium triacetoxyborohydride (1.34 g, 6.32 mmol) was added and stirring continued for 4 hours. The reaction mixture was then washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried (MgSO4) and evaporated under reduced pressure, then the residue purified by chromatography on silica gel, using ethyl acetate: diethylamine (98:2) as eluent, to provide the title compound (2.15 g) as a foam. [α]D25 +9° (c=0.1, CH3OH). Found : C,62.81; H,6.28; N,9.53. C29H34N4O5S; 0.30 H2O required C,62.63; H,6.27; N,10.07%.

Workup

  1. waitcontinued for 4 hours
  2. washThe reaction mixture was then washed successively with saturated aqueous sodium bicarbonate solution and saturated brine
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5e20897001cb4c0c88fed6939ac1e5df
Source dataset
uspto-grants-1999_01
Patent number
US05861393

Reaction notes

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